JPS6129342B2 - - Google Patents
Info
- Publication number
- JPS6129342B2 JPS6129342B2 JP55143572A JP14357280A JPS6129342B2 JP S6129342 B2 JPS6129342 B2 JP S6129342B2 JP 55143572 A JP55143572 A JP 55143572A JP 14357280 A JP14357280 A JP 14357280A JP S6129342 B2 JPS6129342 B2 JP S6129342B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- pyridine
- mmol
- acid
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- -1 propylene, ethylene Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 23
- OYJOLTPPSDAGJC-UHFFFAOYSA-N 2-(pyridin-4-ylmethylsulfanyl)ethanol Chemical class OCCSCC1=CC=NC=C1 OYJOLTPPSDAGJC-UHFFFAOYSA-N 0.000 abstract description 13
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract description 3
- PGTWETKOKSJIQO-UHFFFAOYSA-N 1-(pyridin-4-ylmethylsulfanyl)propan-2-ol Chemical compound CC(O)CSCC1=CC=NC=C1 PGTWETKOKSJIQO-UHFFFAOYSA-N 0.000 abstract description 2
- IIJADHQFJSSMHU-UHFFFAOYSA-N 2-(pyrimidin-4-ylmethylsulfanyl)ethanol Chemical compound OCCSCC1=CC=NC=N1 IIJADHQFJSSMHU-UHFFFAOYSA-N 0.000 abstract description 2
- BAPIUJYONJVSKH-UHFFFAOYSA-N 3-(pyridin-4-ylmethylsulfanyl)butan-2-ol Chemical compound CC(O)C(C)SCC1=CC=NC=C1 BAPIUJYONJVSKH-UHFFFAOYSA-N 0.000 abstract description 2
- ZQADQPAQGWNURI-UHFFFAOYSA-N 3-(pyridin-4-ylmethylsulfanyl)propane-1,2-diol Chemical compound OCC(O)CSCC1=CC=NC=C1 ZQADQPAQGWNURI-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- KHJJJVWKGALGAY-UHFFFAOYSA-N 2-(pyridin-4-ylmethylsulfanyl)phenol Chemical compound OC1=CC=CC=C1SCC1=CC=NC=C1 KHJJJVWKGALGAY-UHFFFAOYSA-N 0.000 abstract 1
- 230000004957 immunoregulator effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000003921 oil Substances 0.000 description 68
- 235000019198 oils Nutrition 0.000 description 68
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 239000003480 eluent Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 230000009467 reduction Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- YUWAUUTYKFAJBH-UHFFFAOYSA-N pyridin-4-ylmethanethiol Chemical compound SCC1=CC=NC=C1 YUWAUUTYKFAJBH-UHFFFAOYSA-N 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 150000004678 hydrides Chemical class 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 239000005909 Kieselgur Substances 0.000 description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 7
- 229960002170 azathioprine Drugs 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 150000004795 grignard reagents Chemical class 0.000 description 7
- 239000007818 Grignard reagent Substances 0.000 description 6
- 239000012981 Hank's balanced salt solution Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 6
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 150000003222 pyridines Chemical class 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
- ZDHKVKPZQKYREU-UHFFFAOYSA-N 4-(chloromethyl)pyridine;hydron;chloride Chemical compound Cl.ClCC1=CC=NC=C1 ZDHKVKPZQKYREU-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000028993 immune response Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 210000003743 erythrocyte Anatomy 0.000 description 4
- 239000002024 ethyl acetate extract Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000012448 Lithium borohydride Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241001494479 Pecora Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- XRDQIFGHTFLEHD-UHFFFAOYSA-N ethyl 2-(pyridin-4-ylmethylsulfanyl)propanoate Chemical compound CCOC(=O)C(C)SCC1=CC=NC=C1 XRDQIFGHTFLEHD-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 230000002519 immonomodulatory effect Effects 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003568 thioethers Chemical group 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MMOWVDUAMKMATM-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-(pyridin-4-ylmethylsulfanyl)ethanol Chemical compound C1=CC(OC)=CC=C1C(O)CSCC1=CC=NC=C1 MMOWVDUAMKMATM-UHFFFAOYSA-N 0.000 description 2
- GHKXFBCTSQWTMO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-(pyridin-4-ylmethylsulfanyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CSCC1=CC=NC=C1 GHKXFBCTSQWTMO-UHFFFAOYSA-N 0.000 description 2
- KAERSUJPVVNCLP-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-(pyridin-4-ylmethylsulfanyl)ethanol Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)CSCC1=CC=NC=C1 KAERSUJPVVNCLP-UHFFFAOYSA-N 0.000 description 2
- QVZYJAXGEHWNMB-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-(pyridin-4-ylmethylsulfanyl)ethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)CSCC1=CC=NC=C1 QVZYJAXGEHWNMB-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- SLHYXNYHQSTFMA-UHFFFAOYSA-N 1-phenyl-2-(pyridin-4-ylmethylsulfanyl)ethanol Chemical compound C=1C=CC=CC=1C(O)CSCC1=CC=NC=C1 SLHYXNYHQSTFMA-UHFFFAOYSA-N 0.000 description 2
- PFMZKLLNBVGYQB-UHFFFAOYSA-N 1-phenyl-2-(pyridin-4-ylmethylsulfanyl)ethanone Chemical compound C=1C=CC=CC=1C(=O)CSCC1=CC=NC=C1 PFMZKLLNBVGYQB-UHFFFAOYSA-N 0.000 description 2
- UKNOHZCPWSXJPL-UHFFFAOYSA-N 1-phenyl-2-(pyridin-4-ylmethylsulfanyl)propan-1-ol Chemical compound C=1C=CC=CC=1C(O)C(C)SCC1=CC=NC=C1 UKNOHZCPWSXJPL-UHFFFAOYSA-N 0.000 description 2
- RDWSWEZQTVXLBM-UHFFFAOYSA-N 2-(pyridin-4-ylmethylsulfanyl)propan-1-ol Chemical compound OCC(C)SCC1=CC=NC=C1 RDWSWEZQTVXLBM-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- DKBVJOOKZMTTMK-UHFFFAOYSA-N 2-methyl-1-(pyridin-4-ylmethylsulfanyl)propan-2-ol Chemical compound CC(C)(O)CSCC1=CC=NC=C1 DKBVJOOKZMTTMK-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- KRLKXOLFFQWKPZ-UHFFFAOYSA-N 4-(bromomethyl)pyridine Chemical compound BrCC1=CC=NC=C1 KRLKXOLFFQWKPZ-UHFFFAOYSA-N 0.000 description 2
- DINNJAVAAQMMHV-UHFFFAOYSA-N 4-pyridin-4-ylbutane-2-thione Chemical compound CC(=S)CCC1=CC=NC=C1 DINNJAVAAQMMHV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000002456 anti-arthritic effect Effects 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- CMJVTGWDYPQSTL-UHFFFAOYSA-N dihydrogen phosphate;2-(pyridin-1-ium-4-ylmethylsulfanyl)ethanol Chemical compound OP(O)(O)=O.OCCSCC1=CC=NC=C1 CMJVTGWDYPQSTL-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 230000002584 immunomodulator Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960001614 levamisole Drugs 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
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- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- ZGXKOLGDFWQRMM-UHFFFAOYSA-N pyridin-4-ylmethyl acetate Chemical compound CC(=O)OCC1=CC=NC=C1 ZGXKOLGDFWQRMM-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- ZFQUWZCCXOTRJG-UHFFFAOYSA-M sodium;2-(pyridin-4-ylmethylsulfanyl)propanoate Chemical compound [Na+].[O-]C(=O)C(C)SCC1=CC=NC=C1 ZFQUWZCCXOTRJG-UHFFFAOYSA-M 0.000 description 1
- GZRBQJHJRPGHAJ-UHFFFAOYSA-M sodium;2-phenyl-2-(pyridin-4-ylmethylsulfanyl)acetate Chemical compound [Na+].C=1C=CC=CC=1C(C(=O)[O-])SCC1=CC=NC=C1 GZRBQJHJRPGHAJ-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01D—HARVESTING; MOWING
- A01D34/00—Mowers; Mowing apparatus of harvesters
- A01D34/001—Accessories not otherwise provided for
- A01D34/003—Means for cleaning the machine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C33/00—Moulds or cores; Details thereof or accessories therefor
- B29C33/56—Coatings, e.g. enameled or galvanised; Releasing, lubricating or separating agents
- B29C33/60—Releasing, lubricating or separating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/68—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts by incorporating or moulding on preformed parts, e.g. inserts or layers, e.g. foam blocks
- B29C70/84—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts by incorporating or moulding on preformed parts, e.g. inserts or layers, e.g. foam blocks by moulding material on preformed parts to be joined
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
- F16C11/00—Pivots; Pivotal connections
- F16C11/04—Pivotal connections
- F16C11/06—Ball-joints; Other joints having more than one degree of angular freedom, i.e. universal joints
- F16C11/0604—Construction of the male part
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
- F16C11/00—Pivots; Pivotal connections
- F16C11/04—Pivotal connections
- F16C11/06—Ball-joints; Other joints having more than one degree of angular freedom, i.e. universal joints
- F16C11/068—Special features relating to lubrication
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Environmental Sciences (AREA)
- Composite Materials (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/085,011 US4246263A (en) | 1979-10-15 | 1979-10-15 | Antiinflammatory and immunoregulatory pyrimidines, their method of use and pharmaceutical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5663962A JPS5663962A (en) | 1981-05-30 |
| JPS6129342B2 true JPS6129342B2 (de) | 1986-07-05 |
Family
ID=22188737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14357280A Granted JPS5663962A (en) | 1979-10-15 | 1980-10-14 | Pyridines as novel antiinflammatory and immune regulant agent |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4246263A (de) |
| JP (1) | JPS5663962A (de) |
| KR (2) | KR840001614B1 (de) |
| AR (3) | AR226864A1 (de) |
| AT (2) | AT377513B (de) |
| AU (1) | AU517763B2 (de) |
| BE (1) | BE885709A (de) |
| CA (1) | CA1156231A (de) |
| CH (1) | CH646425A5 (de) |
| CS (2) | CS226020B2 (de) |
| DD (2) | DD154816B3 (de) |
| DE (1) | DE3038593A1 (de) |
| DK (1) | DK152427C (de) |
| EG (1) | EG14676A (de) |
| ES (2) | ES8201972A1 (de) |
| FI (1) | FI75560C (de) |
| FR (1) | FR2467199A1 (de) |
| GB (2) | GB2061928B (de) |
| GR (1) | GR70311B (de) |
| HK (2) | HK1185A (de) |
| HU (2) | HU183233B (de) |
| IE (1) | IE50665B1 (de) |
| IL (1) | IL61261A (de) |
| IN (2) | IN154554B (de) |
| IT (1) | IT1195269B (de) |
| KE (2) | KE3461A (de) |
| LU (1) | LU82844A1 (de) |
| MY (2) | MY8500323A (de) |
| NL (1) | NL8005652A (de) |
| NO (1) | NO156566C (de) |
| NZ (1) | NZ195246A (de) |
| PH (1) | PH18277A (de) |
| PL (2) | PL125402B1 (de) |
| PT (1) | PT71917B (de) |
| SE (1) | SE437023B (de) |
| SG (2) | SG56384G (de) |
| SU (2) | SU1083907A3 (de) |
| YU (2) | YU41740B (de) |
| ZA (1) | ZA806306B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4371696A (en) * | 1980-07-14 | 1983-02-01 | Pfizer Inc. | Certain pyridine methylthio acetaldehyde derivatives and non-cyclic and cyclic acetals thereof |
| GB8405896D0 (en) * | 1984-03-07 | 1984-04-11 | Sandoz Ltd | Organic compounds |
| EP0311616B1 (de) * | 1986-06-17 | 1991-09-25 | Biogen, Inc. | Kombination von gammainterferonen und antientzündungsmitteln oder antipyretischen mitteln zur behandlung von krankheiten |
| US6878743B2 (en) * | 2001-09-18 | 2005-04-12 | Sunesis Pharmaceuticals, Inc. | Small molecule inhibitors of caspases |
| PL1896401T3 (pl) * | 2005-02-25 | 2014-03-31 | Univ Temple | Synteza nienasyconych siarczków, sulfonów, sulfotlenków i sulfonamidów |
| TW200917961A (en) * | 2007-08-23 | 2009-05-01 | Sumitomo Chemical Co | Fluorine-containing organosulfur compound and pesticidal composition thereof |
| CN108530606B (zh) * | 2018-04-19 | 2020-11-20 | 山东师范大学 | 一种pH敏感性医用聚氨酯脲材料及其制备方法 |
| US11981625B2 (en) | 2018-10-08 | 2024-05-14 | Ecolab Usa Inc. | Sulfide-based compounds and uses thereof |
| CN110483740B (zh) * | 2019-08-12 | 2021-08-27 | 山东师范大学 | 一种聚合物、pH敏感性纳米囊泡及制备方法与应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409626A (en) * | 1963-09-17 | 1968-11-05 | Neisler Lab Inc | Indolylethyl pyridinium quaternary ammonium compounds |
| NL144484B (nl) * | 1967-07-26 | 1975-01-15 | Merck & Co Inc | Werkwijze ter bereiding van een geneesmiddel met anti-anflammatoire werking, alsmede werkwijze ter bereiding van de anti-inflammatoir werkzame aralkylmercaptoaminozuren. |
| US3558640A (en) * | 1967-12-20 | 1971-01-26 | Merck & Co Inc | Certain pyridyl and thiazolyl methylthiopropionic acids and derivatives |
| US3636074A (en) * | 1968-08-05 | 1972-01-18 | Hooker Chemical Corp | Novel mercaptophenol derivatives |
| US3591584A (en) | 1968-08-27 | 1971-07-06 | Pfizer | Benzothiazine dioxides |
| US3818009A (en) * | 1969-12-29 | 1974-06-18 | Lilly Co Eli | Alpha, alpha-disubstituted-5-pyrimidinemethanes |
| US3676463A (en) | 1970-10-15 | 1972-07-11 | Pfizer | Oxobenzofuran carboxamides |
| US3707475A (en) | 1970-11-16 | 1972-12-26 | Pfizer | Antiinflammatory imidazoles |
| JPS52125170A (en) * | 1976-04-12 | 1977-10-20 | Yoshitomi Pharmaceut Ind Ltd | Pyridine derivatives |
-
1979
- 1979-10-15 US US06/085,011 patent/US4246263A/en not_active Expired - Lifetime
-
1980
- 1980-08-16 IN IN597/DEL/80A patent/IN154554B/en unknown
- 1980-09-24 DK DK403080A patent/DK152427C/da not_active IP Right Cessation
- 1980-10-09 AR AR282823A patent/AR226864A1/es active
- 1980-10-10 CA CA000362238A patent/CA1156231A/en not_active Expired
- 1980-10-11 GR GR63147A patent/GR70311B/el unknown
- 1980-10-13 DE DE19803038593 patent/DE3038593A1/de active Granted
- 1980-10-13 IL IL61261A patent/IL61261A/xx unknown
- 1980-10-13 LU LU82844A patent/LU82844A1/fr unknown
- 1980-10-13 AT AT0508980A patent/AT377513B/de not_active IP Right Cessation
- 1980-10-13 YU YU2626/80A patent/YU41740B/xx unknown
- 1980-10-13 GB GB8032971A patent/GB2061928B/en not_active Expired
- 1980-10-13 NZ NZ195246A patent/NZ195246A/en unknown
- 1980-10-13 GB GB8137997A patent/GB2092133B/en not_active Expired
- 1980-10-14 NL NL8005652A patent/NL8005652A/nl not_active Application Discontinuation
- 1980-10-14 BE BE0/202467A patent/BE885709A/fr not_active IP Right Cessation
- 1980-10-14 ES ES495932A patent/ES8201972A1/es not_active Expired
- 1980-10-14 DD DD80224544A patent/DD154816B3/de not_active IP Right Cessation
- 1980-10-14 IT IT25324/80A patent/IT1195269B/it active
- 1980-10-14 JP JP14357280A patent/JPS5663962A/ja active Granted
- 1980-10-14 EG EG80638A patent/EG14676A/xx active
- 1980-10-14 NO NO803073A patent/NO156566C/no unknown
- 1980-10-14 FI FI803239A patent/FI75560C/fi not_active IP Right Cessation
- 1980-10-14 PH PH24725A patent/PH18277A/en unknown
- 1980-10-14 IE IE2125/80A patent/IE50665B1/en unknown
- 1980-10-14 AU AU63240/80A patent/AU517763B2/en not_active Ceased
- 1980-10-14 HU HU802494A patent/HU183233B/hu not_active IP Right Cessation
- 1980-10-14 FR FR8021931A patent/FR2467199A1/fr active Granted
- 1980-10-14 ZA ZA00806306A patent/ZA806306B/xx unknown
- 1980-10-14 SU SU802993951A patent/SU1083907A3/ru active
- 1980-10-14 SE SE8007193A patent/SE437023B/sv not_active IP Right Cessation
- 1980-10-14 HU HU83101A patent/HU191824B/hu not_active IP Right Cessation
- 1980-10-14 PT PT71917A patent/PT71917B/pt unknown
- 1980-10-15 PL PL1980231782A patent/PL125402B1/pl unknown
- 1980-10-15 CH CH771980A patent/CH646425A5/fr not_active IP Right Cessation
- 1980-10-15 PL PL1980227307A patent/PL125314B1/pl unknown
- 1980-10-15 KR KR1019800003966A patent/KR840001614B1/ko active
- 1980-10-15 CS CS806985A patent/CS226020B2/cs unknown
-
1981
- 1981-09-08 CS CS816610A patent/CS226034B2/cs unknown
- 1981-09-16 ES ES505544A patent/ES505544A0/es active Granted
- 1981-11-04 SU SU813349450A patent/SU1144617A3/ru active
-
1982
- 1982-01-18 DD DD82236826A patent/DD202543A5/de not_active IP Right Cessation
- 1982-02-18 AR AR288464A patent/AR227576A1/es active
- 1982-02-18 AR AR288463A patent/AR227089A1/es active
- 1982-12-01 YU YU2668/82A patent/YU42059B/xx unknown
-
1983
- 1983-07-22 AT AT0268783A patent/AT379801B/de not_active IP Right Cessation
-
1984
- 1984-06-05 IN IN464/DEL/84A patent/IN163553B/en unknown
- 1984-08-13 SG SG563/84A patent/SG56384G/en unknown
- 1984-08-22 KR KR1019840005076A patent/KR840001615B1/ko not_active IP Right Cessation
- 1984-09-24 KE KE3461A patent/KE3461A/xx unknown
- 1984-09-25 SG SG691/84A patent/SG69184G/en unknown
- 1984-10-05 KE KE3466A patent/KE3466A/xx unknown
-
1985
- 1985-01-03 HK HK11/85A patent/HK1185A/xx unknown
- 1985-12-30 MY MY323/85A patent/MY8500323A/xx unknown
- 1985-12-30 MY MY325/85A patent/MY8500325A/xx unknown
-
1987
- 1987-09-17 HK HK668/87A patent/HK66887A/xx unknown
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